EP0014547B1 - Fluides résistant au feu - Google Patents
Fluides résistant au feu Download PDFInfo
- Publication number
- EP0014547B1 EP0014547B1 EP80300228A EP80300228A EP0014547B1 EP 0014547 B1 EP0014547 B1 EP 0014547B1 EP 80300228 A EP80300228 A EP 80300228A EP 80300228 A EP80300228 A EP 80300228A EP 0014547 B1 EP0014547 B1 EP 0014547B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fluid
- piperazine
- inhibitor
- phosphate
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- 239000012530 fluid Substances 0.000 title claims description 37
- 230000009970 fire resistant effect Effects 0.000 title claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 17
- -1 phosphate ester Chemical class 0.000 claims description 16
- 230000007797 corrosion Effects 0.000 claims description 11
- 238000005260 corrosion Methods 0.000 claims description 11
- 150000004885 piperazines Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 150000007860 aryl ester derivatives Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 claims description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical group CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical group C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims 1
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical group CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 claims 1
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 claims 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical group CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical group C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 claims 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical group CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical group NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims 1
- NVMHZSCMWYZDCC-UHFFFAOYSA-N bis(4-methylphenyl) phenyl phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=CC=C1 NVMHZSCMWYZDCC-UHFFFAOYSA-N 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical group C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
- HVFKKINZIWVNQG-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)phenol Chemical compound CC(C)C1=CC(C(C)C)=C(O)C(C(C)C)=C1 HVFKKINZIWVNQG-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical compound C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 229940058302 antinematodal agent piperazine and derivative Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009749 continuous casting Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RMNODSGCFHVNDC-UHFFFAOYSA-N phenyl bis(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1 RMNODSGCFHVNDC-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
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- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- This invention relates to fire resistant (difficultly inflammable) fluids based on esters of phosphoric acid. More particularly, the invention relates to a fire resistant fluid based on a phosphoric acid ester or a mixture of phosphoric acid esters and containing a corrosion and hydrolysis inhibitor.
- Hydraulic fluids based on phosphoric acid esters have been used for some time. They have characteristics suitable therefor; particularly, they are not easily inflammable, so that they are used above all in systems comprising closed hydraulic circuits such as hydraulic systems of turbines and of pressure casting, continuous casting and press plants. The use of such fluids is described for example in U.S. Patent 3 468 802 and U.S. Patent 3 723 315.
- a fire resistant fluid comprising a phosphate ester and a corrosion or hydrolysis inhibiting amount of piperazine or a substituted piperazine.
- the fluid of the invention may be useful as a lubricant, a hydraulic fluid, a transformer oil or for a variety of other purposes wherein a fire resistant fluid is required.
- the problem underlying this invention is to develop a fire resistant fluid having improved characteristics compared to those of known fluids used in hydraulic systems, especially with regard to corrosion inhibition and/or hydrolytic stability.
- a fire resistant fluid based on a phosphoric acid ester or a mixture of phosphoric aced esters and containing piperazine and/or at least one piperazine derivative as corrosion and/or hydrolysis inhibitor.
- the proportion of piperazine or piperazine derivative in fluids according to the invention is in the range of 0.005 to 5% by weight and is preferably in the range of 0.01 to 0.5% by weight.
- the phosphate esters used as the base for fire resistant fluids are mainly aryl esters of phosphoric acid.
- the triaryl esters are particularly preferred because they are clearly superior in regard to fire resistance but diaryl alkyl phosphate esters may also be employed.
- the preferred triaryl phosphate esters include, inter alia, tricresyl phosphate ester, trixylyl phosphate ester, phenyl dicresyl phosphate ester, cresyl diphenyl phosphate ester and tri(isopropylphenyl) phosphate ester, di(isopropylphenyl) phenyl phosphate ester and isopropylphenyl diphenyl phosphate ester.
- Diphenyl-2-ethylhexyl phosphate ester is an example of the diarylalkyl phosphate ester which may be used, although with a clear loss of fire resistance in the fluid. If greater fire resistance is required halogenated phosphate esters may be used, in particular chlorinated aryl esters which, however, have considerable other disadvantages (such as corrosion).
- the corrosion and hydrolysis inhibitor may be piperazine itself or a substituted piperazine.
- alkyl, aryl, alkaryl and aralkyl substituted piperazines may be used, and the substituent groups may themselves be substituted, for example, by halogene, hydroxy, alkoxy, amino, alkylamino or dialkylamino groups.
- Other substituent groups on the piperazine ring may be hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxyaryl, amino, aminoalkyl, alkylamino, dialkylamino, alkylaminoalkyl and dialkylamino alkyl.
- the substitution may be made on the carbon or nitrogen atoms of the piperazine ring.
- Preferred types of substituted piperazine are:
- the fluid according to the invention may also include other additives when this is desirable for particular applications.
- additives may be, for example, metal deactivators, antioxidants and antifoaming agents.
- antioxidants are:
- antifoaming agents are silicones.
- Esters A-E are mixtures of the following:
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Lubricants (AREA)
Claims (18)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2903537A DE2903537C2 (de) | 1979-01-31 | 1979-01-31 | Schwer entflammbare Flüssigkeit |
DE2903537 | 1979-01-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0014547A1 EP0014547A1 (fr) | 1980-08-20 |
EP0014547B1 true EP0014547B1 (fr) | 1982-08-04 |
Family
ID=6061752
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80300228A Expired EP0014547B1 (fr) | 1979-01-31 | 1980-01-24 | Fluides résistant au feu |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0014547B1 (fr) |
DE (1) | DE2903537C2 (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10203329A1 (de) * | 2002-01-29 | 2003-08-14 | Bayer Ag | Korrosionsschutzmittel zum Schutz von metallischen Werkstoffen in stark alkalischem Medium |
CN114181757B (zh) * | 2020-09-14 | 2022-06-28 | 安美科技股份有限公司 | 一种磷酸酯抗燃油 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1451301A (fr) * | 1964-05-29 | 1966-01-07 | Shell Int Research | Composition pour la prévention de la rouille |
CA918139A (en) * | 1967-09-06 | 1973-01-02 | J. Shatynski John | Functional fluid composition |
US3398095A (en) * | 1967-11-13 | 1968-08-20 | Shell Oil Co | Vapor-space inhibitors |
US3816311A (en) * | 1971-02-19 | 1974-06-11 | Ethyl Corp | Stable phosphate esters |
US3723315A (en) * | 1971-03-05 | 1973-03-27 | Monsanto Co | Compositions comprising mixtures of substituted triarylphosphates |
US3795621A (en) * | 1971-07-26 | 1974-03-05 | Mc Donnell Douglas Corp | Fire-resistant functional fluids |
US3783132A (en) * | 1972-03-24 | 1974-01-01 | Monsanto Co | Compositions comprising phosphate esters and 2,6-diamino-pyridine as an antioxidant |
US3954873A (en) * | 1972-06-16 | 1976-05-04 | Robert M. Gipson | Amino alcohols |
FR2227319B1 (fr) * | 1973-04-26 | 1979-10-05 | Labofina Sa | |
BE802298A (fr) * | 1973-07-13 | 1973-11-05 | Labofina Sa | Fluides fonctionnels |
US3931023A (en) * | 1974-07-22 | 1976-01-06 | Fmc Corporation | Triaryl phosphate ester functional fluids |
DE2622066A1 (de) * | 1975-05-23 | 1976-11-25 | Cooper Ltd Ethyl | Korrosionsinhibitoren fuer schmieroele |
US4056480A (en) * | 1975-06-10 | 1977-11-01 | Monsanto Company | Hydraulic fluids |
-
1979
- 1979-01-31 DE DE2903537A patent/DE2903537C2/de not_active Expired
-
1980
- 1980-01-24 EP EP80300228A patent/EP0014547B1/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE2903537C2 (de) | 1985-03-07 |
EP0014547A1 (fr) | 1980-08-20 |
DE2903537A1 (de) | 1980-08-07 |
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